1.0 2016-09-30 22:41:00 UTC 2020-04-22 15:06:40 UTC BMDB0001091 BMDB01091 3-Hydroxyquinine 3-Hydroxyquinidine 6'-Methoxycinchonan-3,9-diol 3-Hydroxyquinidine, (3alpha,9S)-isomer 3-Hydroxyquinidine, (8alpha,9R)-isomer 3-Hydroxyquinine C20H24N2O3 340.4162 340.178692644 (3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol 3-hydroxyquinidine 53467-23-5 [H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12 InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20-/m1/s1 BSRUJCFCZKMFMB-ZNYHDOEXSA-N belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety. Organic compounds Alkaloids and derivatives Cinchona alkaloids Cinchona alkaloids 1,2-aminoalcohols 4-quinolinemethanols Alkyl aryl ethers Anisoles Aralkylamines Aromatic alcohols Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organopnictogen compounds Piperidines Pyridines and derivatives Quinuclidines Secondary alcohols Tertiary alcohols Trialkylamines 1,2-aminoalcohol 4-quinolinemethanol Alcohol Alkyl aryl ether Amine Anisole Aralkylamine Aromatic alcohol Aromatic heteropolycyclic compound Azacycle Benzenoid Cinchonan-skeleton Ether Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Piperidine Pyridine Quinoline Quinuclidine Secondary alcohol Tertiary alcohol Tertiary aliphatic amine Tertiary amine Aromatic heteropolycyclic compounds Solid logp 2.24 ALOGPS logs -2.47 ALOGPS logp 1.67 ChemAxon pka_strongest_acidic 13.55 ChemAxon pka_strongest_basic 8.63 ChemAxon iupac (3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol ChemAxon average_mass 340.4162 ChemAxon mono_mass 340.178692644 ChemAxon smiles [H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12 ChemAxon formula C20H24N2O3 ChemAxon inchi InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20-/m1/s1 ChemAxon inchikey BSRUJCFCZKMFMB-ZNYHDOEXSA-N ChemAxon polar_surface_area 65.82 ChemAxon refractivity 95.91 ChemAxon polarizability 36.89 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 301126 Specdb::MsMs 301127 Specdb::MsMs 301128 Specdb::MsMs 343576 Specdb::MsMs 343577 Specdb::MsMs 343578 Specdb::MsMs 2738170 Specdb::MsMs 2738171 Specdb::MsMs 2738172 Specdb::MsMs 2970705 Specdb::MsMs 2970706 Specdb::MsMs 2970707 Specdb::CMs 15858 Specdb::CMs 37923 Specdb::CMs 131579 Specdb::CMs 139313 C07344 FDB022421 138373 441264 17685 2234 3-HYDROXYQUININE Carroll, F. Ivy; Abraham, Philip; Gaetano, Kevan; Mascarella, S. Wayne; Wohl, Ronald A.; Lind, Joan; Petzoldt, Karl. (3S)-3-hydroxyquinidine, the major biotransformation product of quinidine. Synthesis and conformational studies. X-Ray molecular structure of (3S)-3-hydroxyquinidine methanesuiphonate. J. Chem. Soc., Perkin Trans. 1, 1991, 12, 3017-3026